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Author: Subject: Vanillin chemistry: Piperonal
Syn the Sizer
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[*] posted on 27-2-2021 at 16:43


Exactly, the suggested solvents are easy to get, aluminum is no problem to get as is bromine and the aluminum can be doped with a copper salt, doesn't need to be mercury chloride.

here is a video too shared with me a while back.

https://youtu.be/6Uv1NbaITYM
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[*] posted on 27-2-2021 at 18:29


Quote: Originally posted by Benignium  
I read about piperonal turning brown on light exposure on PubChem and always just assumed that the same phenomenon affected my sample, but now I question this. Perhaps once again it's due to impurity. Luckily there is a way to find out.
The piperonal we had in the research lab was stored at room temperature without any apparent deterioration and looked like light cream colored crystals. And yes, it smelled heavenly. I would describe it as cherry-vanilla but with more depth.

[Edited on 2-28-2021 by Texium (zts16)]




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[*] posted on 27-2-2021 at 19:25


@syn--example 2 is activated with copper, and the reaction solvent is xylene. Very doable demethylation, and i've seen the vid you referenced and forgot all about it.



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[*] posted on 27-2-2021 at 21:50


Well, the reaction conditions produced something. Exactly what, is not proven. So, maybe it worked.

As for Heliotropine and Pyridine.... Heaven and Hell?

I haven't had a whiff of Pyridine in ages. God, what a stink! You never forget it.

As for Heliotropine, you can smell it easily enough, in microscopic quantities.

It's not Quite the same, but Piperonal is called Heliotropin, after the flower.

Nice smelling flower it is.

https://www.ilonasgarden.com/heliotrope/



[Edited on 28-2-2021 by zed]
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Syn the Sizer
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[*] posted on 28-2-2021 at 00:52


Quote: Originally posted by arkoma  
@syn--example 2 is activated with copper, and the reaction solvent is xylene. Very doable demethylation, and i've seen the vid you referenced and forgot all about it.


exactly, my thoughts too.
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[*] posted on 28-2-2021 at 04:37


I put a few milligrams of piperonal in my vaping fluid(tobacco scented), it goes along pretty great together with the aromatic virginia tobacco!
Mhmmm... I guess it doubled my daily nicotine dose though :P
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[*] posted on 28-2-2021 at 04:44


Quote: Originally posted by DraconicAcid  
Quote: Originally posted by Benignium  
DraconicAcid - Which ones are you interested in and why, if you don't mind me asking? I checked out a few at random and the acetic acid ester for one sounds like it would make a fantastic addition to a collection of aroma compounds!


Just for smells- methyl and ethyl piperonylate should be nice. Methyl and ethyl piperonate, too (but my hydrolysis of piperine didn't give a very high yield of the acid, so I haven't tried that yet).


Also of interest to those desiring these things for the interesting smells I've seen
that the mdPhMeCOOH is widely available off Alibaba. It should also make some
very interesting smelling esters.
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[*] posted on 28-2-2021 at 17:30


Thank you, Syn the Sizer, for bringing up this approach. I did actually see this video while planning for the reaction but have since forgotten all about it.

I think I'll try that next since I already have all the necessary reagents, and save the pyridine for something different.


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[*] posted on 28-2-2021 at 19:12


Quote: Originally posted by draculic acid69  
Quote: Originally posted by DraconicAcid  
Quote: Originally posted by Benignium  
DraconicAcid - Which ones are you interested in and why, if you don't mind me asking? I checked out a few at random and the acetic acid ester for one sounds like it would make a fantastic addition to a collection of aroma compounds!


Just for smells- methyl and ethyl piperonylate should be nice. Methyl and ethyl piperonate, too (but my hydrolysis of piperine didn't give a very high yield of the acid, so I haven't tried that yet).


Also of interest to those desiring these things for the interesting smells I've seen
that the mdPhMeCOOH is widely available off Alibaba. It should also make some
very interesting smelling esters.


Is that phenylacetic acid? I made a small amount of that a year or so ago, but didn't turn it into an ester (yet). I'd also like to find an easy way to turn cinnamic aicd into hydrocinnamic acid......

[Edited on 1-3-2021 by DraconicAcid]




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[*] posted on 28-2-2021 at 19:37


Quote: Originally posted by DraconicAcid  
Is that phenylacetic acid?

Homopiperonylic acid, I believe:
https://www.sigmaaldrich.com/catalog/product/aldrich/329673?...

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DraconicAcid
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[*] posted on 28-2-2021 at 20:00


Quote: Originally posted by Benignium  
Quote: Originally posted by DraconicAcid  
Is that phenylacetic acid?

Homopiperonylic acid, I believe:
https://www.sigmaaldrich.com/catalog/product/aldrich/329673?...


Ah, that makes sense. And yes, Alibaba has it for $10/kg ($6/kg if you're buying more than 100 kg at once).

I may get the college to start ordering all the chemicals I want to play with from there....




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[*] posted on 28-2-2021 at 21:34


Quote: Originally posted by karlos³  
I put a few milligrams of piperonal in my vaping fluid(tobacco scented), it goes along pretty great together with the aromatic virginia tobacco!
Mhmmm... I guess it doubled my daily nicotine dose though :P


Interesting, I am curious about the taste as well.

Quote: Originally posted by draculic acid69  

Also of interest to those desiring these things for the interesting smells I've seen
that the mdPhMeCOOH is widely available off Alibaba. It should also make some
very interesting smelling esters.


Yes, I had heard about that, but I forgot they had it, thanks man.

Quote: Originally posted by Benignium  
Thank you, Syn the Sizer, for bringing up this approach. I did actually see this video while planning for the reaction but have since forgotten all about it.

I think I'll try that next since I already have all the necessary reagents, and save the pyridine for something different.



Np man, I knew I had it but didn't think to mention it until I got home and found the paper.
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[*] posted on 28-2-2021 at 21:49


(As an aside, how is Alibaba for buying small quantities? Such as shipping rates? I've only used AliExpress.)



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[*] posted on 1-3-2021 at 04:02


Quote: Originally posted by DraconicAcid  
Quote: Originally posted by draculic acid69  
Quote: Originally posted by DraconicAcid  
Quote: Originally posted by Benignium  
DraconicAcid - Which ones are you interested in and why, if you don't mind me asking? I checked out a few at random and the acetic acid ester for one sounds like it would make a fantastic addition to a collection of aroma compounds!


Just for smells- methyl and ethyl piperonylate should be nice. Methyl and ethyl piperonate, too (but my hydrolysis of piperine didn't give a very high yield of the acid, so I haven't tried that yet).


Also of interest to those desiring these things for the interesting smells I've seen
that the mdPhMeCOOH is widely available off Alibaba. It should also make some
very interesting smelling esters.


Is that phenylacetic acid? I made a small amount of that a year or so ago, but didn't turn it into an ester (yet). I'd also like to find an easy way to turn cinnamic aicd into hydrocinnamic acid......

[Edited on 1-3-2021 by DraconicAcid]


Yes it's the mdphenylacetic.
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[*] posted on 1-3-2021 at 04:07


Quote: Originally posted by DraconicAcid  
(As an aside, how is Alibaba for buying small quantities? Such as shipping rates? I've only used AliExpress.)


No idea.ive only bought plastic resins off Alibaba. I'd recommend AliExpress if possible as my experience was slow and not painless. Experience with AliExpress was way smoother
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[*] posted on 1-3-2021 at 05:54


It's not too bad, personally I take a lot of time when looking for supplies because pricing is always a mystery. You can get good deals for small quantities, but you may still end up paying twice that for shipping (real example: 50 grams/60 USD + 100 USD shipping). Because most of the listed prices are not accurate, you will have to speak to the supplier anyway and may as well ask for a sample quantity or just a smaller order. Many will work with you. It really depends on what you're looking for too, and how you present yourself when speaking with suppliers.



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[*] posted on 1-3-2021 at 17:56


I have heard with Alibaba the best thing to do is contact several sellers for pricing. Some may send samples as well. Find the best pricing and let the other sellers know you found a better price and they sometimes lower their prices to get you business, same as dropping quantities.

Some may have a min order of 10Kg and another 500g but a higher price, so they may drop down to 1000g for the same price. This example is just speculation but when a seller is buying 100Kg+ for a great price, they sometimes really work with you.

I have had non Alibaba sellers change quantities and whatnot to keep my business.

I have no first hand experience, this is just a word of mouth thing from others who have ordered.

Syn'

[Edited on 2-3-2021 by Syn the Sizer]
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[*] posted on 6-3-2021 at 12:44


Quote: Originally posted by DraconicAcid  
I'd also like to find an easy way to turn cinnamic aicd into hydrocinnamic acid......


OrgSyn describes a electric reduction method that seem quite easy for making hydrocinnamic acid from cinnamic acid.
The porous cup can be an unglazed clay flowerpot if you can find one without hole in the bottom.

Look at Orgsyn, Collective Volume, 1, p. 311.
Or view the PDF

Attachment: Hydrocinnamic acid - Orgsyn.pdf (316kB)
This file has been downloaded 119 times

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[*] posted on 6-3-2021 at 12:54


If you buy a quantity below a kilo(usually), you will probably pay still almost the same price.
Usually it only pays off if you buy a kilogram at least, which is standard there for almost every chemical.
Otherwise you will face prices like for 100g 3/4th of the price of a whole kilo and such.
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[*] posted on 6-3-2021 at 13:38


Quote: Originally posted by Syn the Sizer  
I finally got the time to actually find the patent.

This demonstrates a method of demethylating vanillin using aluminum bromide produced in situ from elemental bromine and elemental aluminum in an variety of aryl solvents. They boast a ~90% yield.
They explain the advantages over other methods.


Everything old is new again:
http://www.sciencemadness.org/talk/viewthread.php?tid=92847&...




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 6-3-2021 at 13:45


Quote: Originally posted by Mateo_swe  
Quote: Originally posted by DraconicAcid  
I'd also like to find an easy way to turn cinnamic aicd into hydrocinnamic acid......


OrgSyn describes a electric reduction method that seem quite easy for making hydrocinnamic acid from cinnamic acid.
The porous cup can be an unglazed clay flowerpot if you can find one without hole in the bottom.

Look at Orgsyn, Collective Volume, 1, p. 311.
Or view the PDF


Yes, I know that method, but mucking around with a mercury electrode doesn't fit my definition of easy. Thanks anyway.




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[*] posted on 6-3-2021 at 19:54


DraconicAcid,

If you have nickel chloride and zinc dust at hand, your desired reduction will proceed quite nicely. I have been doing several of the cinnamate reductions recently and they work very well if you do not mind a bit of inorganic waste. I have been using the procedure in

Nose and Kudo, Chem. Pharm. Bull. Japan, 38, 2097 (1990).

I have been running the reactions on a 10 mmole scale using the procedures described in the paper. My isolated yields are all >90% and the reduction is complete based on the permanganate spot test of the isolated products. I prefer reducing the cinnamate methyl esters as the work up is more convenient.

This is not the most "modern" of reductions but it works, reagents are readily available and it is easily adaptable to the hobby lab.

Hope this helps.

AvB
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[*] posted on 6-3-2021 at 20:13


Quote: Originally posted by AvBaeyer  
DraconicAcid,

If you have nickel chloride and zinc dust at hand, your desired reduction will proceed quite nicely. I have been doing several of the cinnamate reductions recently and they work very well if you do not mind a bit of inorganic waste. I have been using the procedure in

Nose and Kudo, Chem. Pharm. Bull. Japan, 38, 2097 (1990).

I have been running the reactions on a 10 mmole scale using the procedures described in the paper. My isolated yields are all >90% and the reduction is complete based on the permanganate spot test of the isolated products. I prefer reducing the cinnamate methyl esters as the work up is more convenient.

This is not the most "modern" of reductions but it works, reagents are readily available and it is easily adaptable to the hobby lab.

Hope this helps.

AvB


Some papers also claim Cu/Zn couple can also achieve the same reduction in good yield: DOI:10.1039/P19830001219 . I also remember something ab a dithionite system working too, but I cant seem to find the relevant paper.
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